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Abstract

Charge-transfer salts of tetrathiafulvalene, its selenium analog and its substituted derivatives (1) are among the most electrically conducting organic solids presently known. The key synthetic step in preparing these tetrathiafulvalene donors involves the coupling of compounds such as 2. (Image Omitted)

Country

United States

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English (United States)

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Use of Sodium Benzyl Selenodithicocarbonate for the Preparation of
Selenocarbonyl 1 3 Dithiole and 1 3 Diselenole Derivatives

Charge-transfer salts of tetrathiafulvalene, its selenium analog and its
substituted derivatives (1) are among the most electrically conducting organic
solids presently known. The key synthetic step in preparing these
tetrathiafulvalene donors involves the coupling of compounds such as 2.

(Image Omitted)

While a variety of synthetic procedures are aVailable for coupling compound
2; most of these methods depend very much on the nature of the heteroatom (X
and Y) and the R substituent.

The most general coupling method appears to be the use of phosphorous
bases to couple 2. In fact, this procedure is the only means capable of preparing
selenium TTF derivatives (X = Se). For unsubstituted systems (R = H) when Y =
S, this coupling reaction does not work.

Only when Y = Se does the reaction work well. The reason for this is
undoubtedly due to the weaker C=Se bond which can be more easily broken,
under milder reaction conditions. This quality of the C=Se, also typically leads to
better yields and more easily isolated products for the substituted derivatives of
TTF.

Unfortunately, most syntheses of 2 lead to a thiocarbonyl and good synthetic
methods for converting C=S to C=Se are lacking. A new synthetic procedure for
preparing selenocarbonyl derivatives of 2 starting from elemental selenium is
hereafter described. This method uses the new reagent:...